I have a habit of showing up late to see movies at the Music Box with a bag of greasy empanadas hidden in my purse. I quickly duck into the Argentinian mercado up the block before heading into the theater. The secrecy involved in bringing them into the theater and eating them in the dark makes the ritual seem like something only I know about.
Recently I mentioned my empanada & movies combination to my roommate and she told me she’s done the same thing. I’m floored! We share this love for greasy meat and cheese pies. It bonds us. Until it becomes clear as she describes sometimes sitting down at the restaurant to eat empanadas that we are not talking about the same place. I go to the Argentinian mercado on the corner of Southport and Grace, she is talking about 5411 Empanadas, also on Southport. Neither of us has eaten at the other empanada place, but we suspect that our empanada shop is better than the other’s. We agree to disagree, politely because we are sure that even the inferior empanadas are still delicious.
Several weeks pass and I am delightfully eating some empanadas at my desk at work, an indulgent breakfast treat. My boss notices, a grin spreads on his fast. “Did you stop at Cafe Tola?” He recounts a happy routine he had years ago of getting Cafe Tola empanadas whenever he checked his PO box at the nearby post office. The tone of his voice tells me the way he feels about his post office-empanada tradition is similar to how I feel about my Music Box-empanada nights.
How can a two-block stretch have three highly recommended options for empanadas? What if my initial choice to go to the Argentinian mercado was wrong and I am missing out on better empanadas each time I go back? There is only one reasonable response to these questions. I embark on an objective taste test.*
5411 Empanadas
The Southport Corridor location is the newest storefront for this chic casual eatery that has two Wicker Park locations, a counter serve spot in the Loop, another Lakeview restaurant, and a food truck.
5411 Empanadas. I can still wear children's ski mittens to give you a hand size estimate.
Hours:
Mon - Thurs 11:00 a.m. to 9:00 p.m.
Friday 11:00 a.m. to 11:00 p.m.
Saturday 9:00 a.m. to 11:00 p.m.
Sunday 9:00 a.m. to 9:00 p.m.
Location: 3715 N. Southport Ave.
Vibe: Casual chic -- you order at the counter and they bring the food out to you. It’s small, quiet with sidewalk seating, and a clean, modern feel.
Price: Around $2.50/empanada.
Size: They’re the smallest, but not the most expensive, so dollar per bite, they’re competitively priced. Four empanadas was a filling meal and it cost somewhere around $11 with tax.
Sweet corn from 5411. This is a traditional Argentine filling.
Review: 5411 bakes their empanadas, and there are a multitude of varieties to try. I had the patatas bravas and chorizo, which was a bit dry. The mushroom and blue cheese was a nice veggie option and had a lovely gooeyness and umami tang to it. I was underwhelmed by the consistency of the ham and cheese. The filling was a bit too thick. The sweet corn was pretty tasty! I regret not getting the Malbec beef. It seems like their signature item. Ugh, I guess I’ll have to go back. This was the only empanada restaurant that had seating and it felt like it was the healthiest choice due to the empanadas’ size and baked crust. The empanadas were definitely Argentinian style and the restaurant had an argentine feel as well. 5411 doesn’t win the Southport empanada smackdown despite having the best menu with the most options and most interesting combinations. Of the four I sampled, none were outstanding
Cafe Tola
This place is beloved and well established in the neighborhood. It’s known for having the “best empanadas” in the city. Please understand the dual purpose of my quotations-- this is a common title applied to the restaurant, but I’m also mocking this description because who am I to trust what most people think? Was there a citywide vote? Regardless, it has a quirky vibe and tons of fun coffee drinks and baked goods. There’s a table outside if you want to eat your empanada and watch the world pass by.
Big mambo jambo empanadas at Cafe Tola.
Hours:
Mon - Tues 6:30 a.m. - 7:00 p.m.
Wed - Sun 6:30 a.m. - 8:00 p.m.
Location: 3612 N Southport Ave
Vibe: Counter-serve eclectic tattoo artist grandma urban cottage
Price: $4, the most expensive
Size: The biggest, two will leave you happily stuffed.
The shredded chicken from Cafe Tola is succulent and the texture is delightful.
Review: These are fried and they’re definitely the least traditional of the empanada options (they have a Buffalo Chicken empanada). I loved the shredded chicken which was really juicy and tasty. I did not enjoy the black bean and goat cheese. I love beans, and goat cheese is one of the few reasons I wake in the winter months, but I didn’t think much of this empanada. It had a sweetness I did not care for, and the method of having the cheese stuck in one section made me want to just eat the cheese and chuck the sweet tasting beans. There are other kinds that might have been a safer choice, and the chicken empanada was so good that I’ll definitely go back. The rest of their menu was exciting and creative. I might go back and not get empanadas next time.
El Mercado Food Mart
An Argentinian family runs this small market and butcher shop. They’re the family behind Tango Sur, arguably one of the best BYOBs in the city, Barra N and Folklore. This market is a chance to get restaurant quality Argentine treats for a very reasonable price. There’s nowhere to sit, so don’t plan on eating anything there.
el carne dulce, oh mama!
Hours: Mon - Sat 9:00.m. - 8:00 p.m., Sun. 9:00 a.m. - 5:00 p.m. (according to Google maps).
Location: 3767 N Southport (Southport and Grace).
Vibe: Like an Argentine 7/11 with a small butcher counter, case of steaming hot empanadas, and table of delicate cookies and baked goods.
Price: Empanadas are around $2.
Size: Medium sized, smaller than Cafe Tola, but larger than those at 5411. Three will fill you.
Eggplant empanada from el mercado
Review: Like the prodigal son returning home, I saved the best for last. These are very traditional Argentinian empanadas. They have both baked and fried options, and the varieties are the same every day. Though the choices aren’t as exciting as the other two restaurants, the flavor, texture, and consistency of these empanadas is superior. The eggplant is the best vegetarian 
option in my mind, but spinach isn’t bad either, and there’s a mushroom one that’s pretty good as well. The sweet beef is unreal. The chicken empanada is not as good as the one at Cafe Tola. They have a few dessert empanadas as well. This empanada stop is the most affordable and has the best hours as well. These tasty little pies are always hot and delicious, no matter which variety you try.
Empanada Ruminations
I tried to be as objective as possible with this taste test. I went to each with a full appetite and tried both vegetarian and meaty options. None were thrown out. If I wanted to sit down, I would go to 5411, and if I wanted to get coffee too I would go to Cafe Tola. But for the best empanadas, the mercado is the clear choice.
My final thoughts are these:
Is it possible to objectively do a taste test if you’ve established a routine or ritual surrounding one particular establishment? If my boss or my roommate did the same “objective” taste test, would they ultimately choose the place they’d gone to first and grown to love before they knew about the other choices?
Are empanadas as potentially divisive or unifying as pizza? Like with pizza preference, can empanada preference describe your identity and where you’re from, if you’re casual or classy, modern or traditional? Pizza is a shared meal. Friends or families gather around a pizza, slice it and eat together. Whether that pizza is from Little Caesars or made from scratch and grilled in a wood-fire oven says something about the family, their class, their geographic home, their taste, and how they like to spend their time together. But empanadas are designed as an individual experience unless eaten as an appetizer. Your taste in empanadas says more about you as an individual. If pizza preference shows how you like to socialize and share, than empanada preference shows how you like to eat when you’re alone.
*I only considered the three Southport Corridor empanada options. There are clearly a multitude more choices out there in this fair city, but if I was going to eat every empanada in the city I’d likely fall prey to coronary heart disease and never get to writing this summary. I excluded breakfast and dessert varieties, which I’m sure can be very delicious, but I thought including them might force the comparison to ask too many questions. 